Becoming Samantha
by xephwrites
Summary: Dean discovers Sam's little secret. Set before Dean's Girl. WARNINGS: Wincest, underage Sam is 15 , crossdressing.


Sam tried very hard to concentrate on the notes and books spread out between him and his friend Amanda. It was difficult to study with her constant annoyed sighs.

"I'm never going to get this!" She said, throwing her pen down to the pile of paper. Sam straightened and looked her in the eyes.

"You will." He assured softly. "You're very smart. It will make sense." She huffed and flicked her hair off her shoulder. She flopped backwards onto her bed.

"Don't understand why we need to learn this crap in the first place." She crossed her arms across her chest. "Why don't they teach us useful math, like taxes, exchange rates, things we can use. When the hell am I ever going to use algebra?" Sam chuckled at her.

"You realize you've said that about every class we have?" Sam held up his hand and ticked off on his fingers. "Geography, French, English, history. Do I need to continue?" She huffed again and sat up.

"I'm going to get a sandwich. Want one?" She swung her legs off the bed and stood up. Sam shook his head and turned back to his books. "Whatever. I offered." She threw over her shoulder as she made her way out of her bedroom. Sam's stomach did a flip as she closed the door.

He waited for a few seconds, enough time for her to turn back. When she didn't, he bolted off the bed and went to her closet. He carefully opened the door and looked inside. Her clothes were all neatly hung, and had a mild potpourri smell. He ran his hand over the various fabrics, imagining how they would feel against him. Towards the back of the rack, he found his prize. He carefully plucked it off the hanger and closed the door. He sprinted back to the bed and shoved the item into the bottom of his backpack. His heart was racing, nervous and excited as he settled himself back on Amanda's bed.

He couldn't wait to finish this study session and get back to the motel.

***

Dad was on a hunt, and Dean was nowhere to be found when Sam got back to the motel they currently called home. At least this one was nicer than most. He slipped into the bathroom with his backpack. He set the overstuffed bag on the closet toilet lid. Carefully unzipping the bag and sorting through books, he found what he stole from Amanda's closet. He pulled it out of the bag, held it up to admire it.

It was a light blue silk knee length sundress. It had spaghetti straps and a very low back. If it were a fraction smaller and had a bit of lace, it could be considered a negligee. Heat worked its way through Sam's body as he laid it carefully over the backpack and began to undress. His stomach clenched nervously. He's only thought about doing this before, not actually done it. Sam hoped that it would feel as good as he thought. As he was stepping out of his jeans, he thought about how happy and carefree girls looked in these types of dresses, and hoped that just by wearing one he could feel the same.

Now naked, he unzipped the back of the dress and slid it on over his head. He reached behind and tugged up the zip. It hugged his chest slightly, and hung perfectly on him. He turned to look at his reflection, and it took his breath away. With just a hairclip, maybe a bit of makeup, he could actually pass as a girl. His dick gave an interested twitch against the fabric, causing him to moan. The silk felt better than he had imagined it, and gave a quick twirl. The dress swished around his body and he laughed. It had been so long since he felt happy.

He was so wrapped up in laughing and staring at his reflection, he didn't hear the door to the motel room shut. He was leaning on the counter, blowing kisses to himself when Dean swung the door open. Sam froze in horror as he saw Dean's surprised expression in the mirror. The silence lasted for a few brief seconds.

"Get out!" Sam yelled, pushing Dean out of the bathroom. He slammed the door and curled into himself leaning against the wood.

"Sammy!" Dean called, knocking on the door. "Sammy, come on, let me in!"

"No!" Sam sobbed. He began to cry at the shame of being caught, by Dean of all people. Dean loved nothing more than to torment him about anything and everything. His stomach tightened and he felt like he would throw up.

"Sam, please." Dean said softly.

"Leave me alone! I don't need you picking on me!" Sam sank to the floor, trying to calm his breathing. He heard Dean sigh on the other side of the door.

"Please, just open up." Sam could hear the sincerity in his voice. "I promise that I'm not going to make fun of you at all."

"Seriously?" Sam choked out.

"Seriously." Dean said back. Sam stayed on the floor and moved away from the door. He curled into a ball in front of the sink. He heard Dean open the door. His stomach threatened to heave out all of its contents. Sam took a deep breath, readying himself for the ridicule he was sure to receive. But Dean said nothing, just sat on the edge of the tub. His tears eased up, but he was still panicking.

"Why aren't you making fun of me?" Sam snapped. "Go on, I know you're just dying to!"

"I'm not." Dean said gently. Sam's head snapped up, looking warily at his brother. Dean held his hands up. "I'm not going to tease you at all." Sam's brows knitted together.

"Really? Just like that, you're not going to bother me?" Sam couldn't help but keep the uncertainty out of his voice. Dean offered a small smile.

"Just like that." Dean gave a quick look to his watch. "Want dinner? I grabbed some pizza." Sam wiped his eyes with the heel of his hands. He reached for his jeans. "You don't have to change, if you don't want." Dean added quickly. "I mean, if you're comfortable….." Sam smiled slightly.

"Thanks, Dean." He said as he stood up off the floor.

***

A few days went by, and neither brought up the dress incident. Sam had kept it tucked away in his duffel, wrapped in an old flannel shirt. He didn't want to risk Dad finding it. At school, Amanda kept tossing odd glances his way, but never talked to him.

Sam was surprised to find that Dean was waiting at the motel for him when he finished school one day. Dean was sitting on the hood of the Impala.

"Chuck your backpack in the motel and let's go." Dean said, hopping off his car. Sam looked questioningly at him. "You want to go out for a ride, or do you want to sit inside the crummy motel by yourself?" Sam unlocked the door, tossed his bag inside, checked the salt lines then shut the door. Dean had the passenger door open for him.

"Where we going?" Sam asked, reaching for the radio dial.

"Next town over." Dean said as he slapped Sam's hand away. Dean relaxed as they pulled away from the motel and down the long road headed west out of town. Sam got comfortable in the seat and stared out the window.

They were only on the road for about twenty minutes before they pulled into a small town, identical to the one they were currently staying in. Dean found a parking spot on a side street. They exited the car and Dean pointed up the street.

"There." He said, walking away from the Impala. Sam followed quickly. He glanced up at the storefronts. Dean stopped in front of a thrift store and reached for his wallet. "Gotta hit a store a bit further up." Dean handed Sam a few twenty dollar bills. "Buy whatever you want. Meet you back here in a half hour." Sam took the money. Dean held his hand briefly. "Honestly, Sam. Anything you want." Sam smiled, realizing what it was Dean meant.

"Thank you." He said softly. Dean ruffled his little brother's hair before walking further up the street. Sam pushed his hair back in place and headed into the thrift store.

A half hour later, they met back at the Impala. Sam clutched a large bag, and Dean had a much smaller one. They got back into the Impala and headed back to the motel.

"What did you get?" Dean asked peeking over at the bag between Sam's feet. Sam pulled the bag a bit closer to him. Dean chuckled. "Its fine, you don't have to tell me."

"The lady at the store was really nice." Sam almost whispered. "I told her I was buying stuff for my sick sister." Sam picked at a small hole in his jeans absently. Dean nodded. "What did you buy?"

"It's a surprise." Dean said. He gave a sideways look at his brother and took a deep breath. "I don't have any issues with you wanting to do this." He blurted out. "I just-I want you to be happy, you know? I need to make sure that you're okay." Sam was staring out the window, nodding at Dean's words.

"Thank you." Sam whispered. "We good?"

"We're good." Dean said. The rest of the car ride back to the motel was in comfortable silence. They both took their packages into the motel room. Sam kept clutching his bag, looking at the bathroom door. Dean waved him in that direction.

"Go on, try your stuff on." Dean said, turning on the television. Sam bolted to the bathroom. Sam had spent a good twenty minutes in the bathroom before he came out. Dean's jaw dropped as his brother stepped into the room, blushing lightly.

"Do I look okay?" He asked quietly. Sam was wearing a purple tank top with a butterfly print on it and a knee length black cotton skirt. Sam crossed his arms across his chest shyly.

"Sam," Dean started. "You're – you're beautiful." Dean's voice had a touch of awe to it. Sam reddened even more and he bit his lip. Dean grabbed the bag of things he bought earlier and reached into it. He pulled out a small silver barrette and a tube of pink lip gloss. He motioned for Sam to come over to where he was sitting on the couch. Dean couldn't help but watch the way the skirt swirled around his brother's legs. Sam sat down beside him, still blushing. Dean took a tiny lock of his brother's dark brown hair and pushed it off his forehead. He held the lock back and slid the silver barrette in place. He held out the tube of lip gloss. Sam looked questioningly at Dean, who shrugged and gave a half smile. "I'm not good at doing that. You give it a shot." Sam smiled, grabbed the lip gloss and ran to the bathroom. A minute passed before Sam stepped out of the bathroom, lips shining with a hint of pink. Dean froze.

His brother Samuel was no longer in the motel room with him. Instead a beautiful young girl was smiling and walking towards him. She sat beside Dean and looked up at him with beautiful hazel eyes. Dean kept his breathing as even as possible and just stared. Dean's hand came slowly up to touch a lock of dark brown hair that was not held by the barrette. He pushed it off Sam's face, but his hand lingered, as if he was afraid to move it in any direction.

"Sammy." Dean whispered as his hand lightly touched the side of his brother's face. Sam's glossy lips parted. Dean leaned forward slightly. "Sammy, stop me." He whispered desperately. Dean moved forward a fraction more. "Please Sam." Sam exhaled loudly and closed the distance between them. Their lips met softly, and Sam moaned into Dean's mouth. Dean's tongue sneaked out and brushed lightly against his brother's pouty bottom lip. Sam's lips had a faint taste of cherry to them. The hand resting on the side of Sam's face slid to the back of his head. Sam tilted his head to deepen the kiss. As Sam parted his lips to take in his brother's tongue, Dean pulled back slightly.

"I'm sorry." Dean whispered against Sam's shiny lips. "I shouldn't." Sam shook his head.

"It's okay. I like this." He placed a small kiss to Dean's bottom lip. "I want to be your girl. I want to be your Samantha." Dean nodded.

"My girl. My Samantha." Dean pulled Sam in for another heated kiss.


End file.
